Tetrahydrofuran → HCID 15839665, Verbindung

HRID 363526Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 363526
[C:1]([C:3]1[CH:18]=[CH:17][C:6]([CH2:7][N:8]2[C:12]([CH2:13][C:14]([NH2:16])=[S:15])=[CH:11][N:10]=[CH:9]2)=[CH:5][CH:4]=1)#[N:2].C1COCC1.[CH3:24][N:25]1[CH:29]=[CH:28][CH:27]=[C:26]1[C:30](=O)[CH2:31]Br>CCOC(C)=O>[C:1]([C:3]1[CH:18]=[CH:17][C:6]([CH2:7][N:8]2[C:12]([CH2:13][C:14]3[S:15][C:30]([C:26]4[N:25]([CH3:24])[CH:29]=[CH:28][CH:27]=4)=[CH:31][N:16]=3)=[CH:11][N:10]=[CH:9]2)=[CH:5][CH:4]=1)#[N:2]

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 124077412-Bromo-1-(1-methyl-1H-pyrrol-2-yl)ethan-1-oneHCID 53772023HCID 53772023, Verbindung

Produkt 1

HCID 15839665HCID 15839665, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a 25 mL round bottomed flask with a stirring bar reflux condenser and an argon inlet is added 1-(4-cyanobenzyl)-5-(aminothiocarbonyl)methyl-1H-imidazole (0.12 g, 0.468 mmol), dry THF (10 mL), and N-methyl-a-bromoacetylpyrrole (0.098 g, 0.491 mmol). This mixture is heated at 50° C. for 7 hours. The cooled reaction mixture is diluted with EtOAc and washed sucessively with aq. NaHCO3, water, and brine. The organic extract is dried, (MgSO4) and the solvent is evaporated in vacuo. The residue is purified by chromatography to afford the title compound.

Aufarbeitung

  1. temperatureTo a 25 mL round bottomed flask with a stirring bar reflux condenser and an argon inlet
  2. customThe cooled reaction mixture
  3. washwashed sucessively with aq. NaHCO3, water, and brine
  4. extractionThe organic extract
  5. customis dried
  6. custom(MgSO4) and the solvent is evaporated in vacuo
  7. customThe residue is purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ec83389ff2e9450381e7f7d96dca43f4
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05874452

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